Guest house holiday rentals in Chesil Bank

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Top-rated guest house rentals in Chesil Bank

Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

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Top guest favourite
Guest house
4.99 out of 5 average rating, 105 reviews

A stylish one-bedroom barn adjacent to a stream.

Developed to a high standard, Streamside sits on the edge of a quiet village, in a picturesque Conservation Area in an AONB. It is ideally situated to explore the Jurassic Coast with countryside walks/cycles via footpaths/bridal ways/turbaries from the door. With views of rolling fields in all directions and the fabulous Kings Arms Pub less than 50m away (roaring fires, wholesome food and great beer), Streamside also benefits from a private patio and a shared garden to relax and enjoy the stream

Top guest favourite
A spacious living area features a cozy sofa facing a wall-mounted television and an electric fireplace with a soft blue glow. Natural light filters through the window, while a dining table and chairs are visible in the background.
Guest house
4.97 out of 5 average rating, 385 reviews

Coast, countryside and towns at your fingertips

Recently refurbished one bed accommodation suitable for up to four people (and one well behaved dog) but please note 3rd and 4th guest will be using the sofa bed in the living room. Use of the wc and shower is accessed via the main bedroom. Plenty of storage for our guests is available and there is a large patio area with barbecue and table and chairs for your sole use. There is also one off road parking space available. We have great links to the Jurassic coast, market towns and Country walks

Top guest favourite
A modern outdoor decking area is shown, featuring a dining set with four chairs around a glass-topped table. Lush green plants are visible, and the sunny sky is partially filled with fluffy clouds, creating a serene setting for relaxation or al fresco dining.
Guest house
4.96 out of 5 average rating, 142 reviews

Palm Cottage

A good sized modern One bedroom garden annex only a short walking distance to local pub, take away, convenience store & hairdressers with a 20 minute walk into the Town Centre and Beach (£6 - £7 taxi ride) Weymouth is a very popular tourist attraction with numerous high end eating establishments, a superb beach and harbour which are particularly vibrant during the Spring and Summer months, a golf course and a railway station. Only 13 miles from the picturesque Lulworth Cove & Durdle Door

Top guest favourite
A spacious sleeping area features a large tufted headboard in a blue hue. Soft lighting is provided by a pendant lamp, while patterned wallpaper adds texture. Two decorative pillows rest on the bed, and natural light filters in through the window covered by dark curtains.
Guest house
4.94 out of 5 average rating, 318 reviews

Seaside studio cabin minutes from 'secret' beach

Tucked away up an unmade track & five minutes walk from a 'secret' local beach; Cove Cabin is a compact, stylish, private space; perfect for a couple or two companions. On the doorstep of lesser known beaches & gardens but not far from Weymouth's bustling scenic harbour & golden sands. Ideal stop off whilst walking the SW Coast Path. The perfect area for watersports, wild swimming, walking, mooching around the harbour & locality, sampling the local seafood & eateries & just simply relaxing.

Top guest favourite
A charming exterior view of a light blue cottage with a dark roof and two front doors. Neatly trimmed bushes line the pathway, and a small outdoor area is visible. The structure is surrounded by greenery, with a clear blue sky overhead.
Guest house
4.96 out of 5 average rating, 214 reviews

The Yorkshireman @ Piddlehinton

We are so excited about our conversion. Completely self-contained, it is a lovely, light, cosy open space with a well equipped kitchen, modern bathroom and a cool sleeping platform/mezzanine. Piddlehinton is a special place, 20 mins from the Jurassic Coast and 10 mins from Dorchester, in the renowned Piddle Valley, with beautiful walks, views and our award winning pub, The Thimble Inn. We are right next door if you need anything, but if you prefer your privacy, you can be totally separate.

Top guest favourite
The shepherd's hut is framed by lush greenery and flowering plants, featuring a wooden exterior with multiple windows. The rustic charm is complemented by a backdrop of open meadows and rolling hills, inviting a sense of serenity and connection to nature.
Guest house
5 out of 5 average rating, 133 reviews

A retreat for outdoorsy types and ‘dreamers’ alike

A tranquil place in beautiful countryside. This Shepherds Hut, in its own garden, is overlooking a meadow. Designed for relaxation, many quirky furnishings are made by the craftsman owners. This rural region is an under-appreciated delight. Ideal for walking, cycling, painting, historic houses, gardens, Messums Gallery and Wardour castle. Wonderful selection of pubs locally, a choice for each night’s stay. Breakfast is laid out in the orangery, all home made (told it is “scoffable”).

Top guest favourite
A cozy bedroom features a spacious bed covered with a patterned quilt, complemented by soft lighting from bedside lamps. A light-colored armchair sits nearby, and a small round table adds functionality. Natural light enters through a curtained window, enhancing the calming atmosphere.
Guest house
4.95 out of 5 average rating, 104 reviews

Milkwell’s heavenly place

Wake up to the divine sound of rich birdsong- this one bedroom studio is exceptionally comfortable and has a peaceful, stylish atmosphere. It is separate to the main house so you have total privacy and the whole space is yours to be enjoyed. Underfloor heating makes it gloriously warm and inviting, the linen sheets are of the finest quality, and it is in a beautiful valley which has an unusual amount of song birds and owls. It has been designed with peace and comfort in mind.

Guest favourite
An outdoor decking area features a small round table with two metal chairs, surrounded by greenery and flowering plants. A blue pot holds herbs, enhancing the tranquil setting with views of the landscape beyond, complemented by a wooden railing.
Guest house
4.94 out of 5 average rating, 324 reviews

Garden Studio with stunning views, West Dorset.

The Garden Studio is situated at the top of our garden and nestles on the side of Hardown Hill (National Trust). It boasts spectacular views over the Marshwood Vale. Great for countryside walks around the vale and along the Jurassic Coast. Good restaurants and places of interest at nearby historic towns Bridport and Lyme Regis. Lovely beaches close by at West Bay, Seatown, Eype, Charmouth and Lyme Regis. We are approx. 2 miles from Charmouth. The Garden Studio welcomes dogs.

Top guest favourite
Guest house
4.97 out of 5 average rating, 119 reviews

Characterful 2-bedroom cozy cottage with garden

Enjoy a stylish experience at this cozy, centrally-located cozy two-bedroom cottage with modern facilities plus Sky, coffee machine and private garden. Bedroom one has a double bed, bedroom two is a twin with two single beds. Walking distance from shops, cafes, Church Ope beach, cliff paths. Visit Portland to sail, dive, rock climb, bike ride, hike, visit art exhibitions, relax and explore. Unsafe for pre-school kids. Sorry no under 4 years old . No smoking 🚭

Guest favourite
A small room features a double bed dressed in luxury bedding against a pale green paneled wall. A black armchair sits next to a white nightstand, complemented by a small vase of flowers. Light hardwood flooring enhances the room's spacious feel.
Guest house
4.86 out of 5 average rating, 108 reviews

The Penthouse (Small but mighty)

Enjoy a stylish experience at this centrally-located place on the Isle of Portland. So many places to visit and all within a stones throw away from our newly refurbished Penthouse. Guest access- just off the road down a private drive with one parking space directly outside. The space- One small but stylish room with a double bed and luxury bedding. Mini fridge and kettle. En-suite modern bathroom, towels included. Check-in from 16:00pm Check out before 10:00am

Guest favourite
A dining area is seen with a neatly set table adorned with a floral tablecloth. Fresh tulips are placed in a vase, alongside breakfast items. Large windows open to the outside, providing natural light and views of the green landscape beyond.
Guest house
4.95 out of 5 average rating, 244 reviews

Cosy lodge, parking, beautiful setting, Lyme Regis

Relax with the whole family at this peaceful place to stay. One of two properties available, Beech Lodge is situated in a quiet spot with lovely views towards the Devon countryside. It is a five minute drive to Lyme Regis and is near a footpath that takes you via Uplyme along the River Lim for a meandering walk into Lyme's centre. It is an ideal base for exploring all that Devon and Dorset has to offer. Please read our reviews. Guests love staying here.

Top guest favourite
An outdoor courtyard setting is visible, featuring a wooden dining table surrounded by six slatted chairs. A small barbecue is positioned nearby. The stone walls of the barn create a rustic backdrop, complemented by a planter with greenery and a hanging basket of flowers.
Guest house
4.94 out of 5 average rating, 160 reviews

Character Barn in the Heart of Beaminster

Recently renovated, this Grade II listed Barn was originally a grain store and is now a one bedroom, comfortable and cosy retreat set in the heart of Beaminster, a small picturesque town nestled in a natural valley in stunning West Dorset, close to the Jurassic coast. The Barn is very close to all the shops, restaurants, pubs and cafes of Beaminster as well as some of Dorset's best walks, National Trust sites, Jurassic Coast beaches and weekend markets.

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